


The Office Grinch

by thatwriterlady



Series: 25 Days of the Holiday Season [5]
Category: Supernatural
Genre: Attraction, Castiel Has a Crush on Dean Winchester, Christmas, Christmas Party, Dean Winchester Has a Crush on Castiel, Eggnog, Flirting, Fluff, Grumbly Castiel, M/M, Office Party, Sweet, Talking
Language: English
Status: Completed
Published: 2020-12-05
Updated: 2020-12-05
Packaged: 2021-03-09 19:08:36
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,184
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27911275
Author URL: https://archiveofourown.org/users/thatwriterlady/pseuds/thatwriterlady
Summary: It's Christmastime but around Sam Winchester's office, people walk on eggshells around their boss. He's extremely cranky and no one wants to get on his bad side. The office Christmas party is coming up and Sam doesn't know it yet but he's going to bring the one thing that can cheer his boss up: His single older brother, Dean. There are eggnog and Christmas sweaters involved, and the start to something beautiful.
Relationships: Castiel/Dean Winchester
Series: 25 Days of the Holiday Season [5]
Series URL: https://archiveofourown.org/series/2037259
Comments: 10
Kudos: 135





	The Office Grinch

**Author's Note:**

> I hope you enjoy this one. I'm so tired that I'm heading off to bed.

**Dec 5th:**

**_The Office Grinch_ ** **~**

“Don’t,” Becky warned. Sam stopped with his fist mere millimeters from their boss’s closed office door. He dropped his hand and gave her a puzzled look.

“I need to talk to him, I need him to sign off on this.” He held up the papers in his other hand. She dropped her hand from his arm and pointed at the door.

“He’s on a rampage. You’re new here so you don’t know this but he’s pretty scary this time of year. Tread lightly and whatever you do,  _ don’t _ piss him off!”

Inside the office they could hear Castiel yelling at someone. It sounded like he was on the phone.

“Does anyone know why?”

“It has to do with his fiance not showing up to their Christmas wedding a few years back. They’d planned this beautiful winter wedding, it was outdoors in the snow and it would have been perfect, except Balthazar never showed up. Everyone from the office had been invited so we were  _ all _ there to witness it. We all thought maybe there was a car accident or something but no, he’d just skipped out. As far as anyone knows, they’ve never spoken since. It puts him in a super bad mood every December but the closer it gets to Christmas, the worse it gets.” She explained softly. Inside the office Castiel sounded thoroughly pissed off. Now Sam was afraid to knock.

“Does he come to the Christmas party each year?”

“He does, but he sits in a corner brooding and drinking spiked eggnog until someone has to call him an Uber.”

The Christmas party was that Friday after work and he found himself wondering just what it would be like. Did everyone walk around on eggshells? He wanted to go for the raffle and the chance to socialize with his coworkers outside of office hours.

“Don’t worry, he doesn’t ruin the party, he doesn’t yell at us for having fun or anything.” She seemed to be reading his mind.

“Oh, that’s good. I feel bad for him,” He gestured towards the papers in his hand again. They were time sensitive so at the risk of getting yelled at, he knocked.

_ “Come in!” _ Castiel barked.

“Good luck,” Becky patted his back and hurried off. He took a deep breath and opened the door.

“Come in, Sam, and close the door behind you.” Castiel looked and sounded irritated. Sam did as told before approaching the desk.

“I needed you to sign off on these before I send them out.”

Castiel took the papers and quietly went over them while Sam took a seat to wait.

“Did Becky give you raffle tickets?” Castiel asked, catching him off guard.

“Yes she did. I bought a hundred dollars worth.”

“You want that television eh?” There was a smirk on his boss’s lips when he looked up at him. Sam chuckled and shrugged.

“I thought I might give it to my brother if I actually win. Someone broke into his house on Thanksgiving and robbed him. They took everything, even his couch. We think someone was watching his house and waiting for him to go to our parents’ house. Our folks gave him the couch in their basement but that’s about all he has. They even stole all of the presents he spent the last year buying.” 

“Oh, I’m sorry to hear that happened,” Castiel frowned. “I’m glad he wasn’t home though and wasn’t hurt.”

“So are we.” Sam agreed.

“Will you be bringing anyone Friday? Did you check in with Marge so she makes sure there’s enough food? She’s in charge of catering this year. It’s potluck too though, so if you want to bring a dish, feel free.”

“I’m bringing my brother,” He replied.

“The same one you want to win the television for?” Castiel asked.

“Yes. I doubt I’ll win it but, if I do, I think it would be really cool to see his expression when I win, and then turn around and give it to him. He’s a manly man, but he’s not afraid to cry, and I know that will make him cry,” Sam smiled thinking about his brother’s reaction. It wasn’t often he was able to surprise Dean, but once in a while he could. He hoped this would be one of those times.

“Well, I hope you win it then. You’ll have stiff competition from Zach in accounting, he tries to out buy everyone every year and most years he wins. Just be forewarned.” Castiel told him as he went back to reviewing the papers.

“Duly noted.” 

It was only a few minutes later that Castiel was handing him back the papers, this time with his signature.

“Go ahead and send these to the lender.”

Sam took them and after saying goodbye he slipped from the room, quietly closing the door behind himself. He was starting to think maybe Becky had been over exaggerating, but then Castiel was yelling again at someone on the phone. All he knew was that he was glad it wasn’t him.

@@@@@@@@@@@@@@@@@@@@@

“So this is where you work?” Dean straightened his tie as they stepped out of the elevator.

“I work downstairs. This floor is where they host parties, at least that’s what I was told,” Sam replied. They’d left their coats in the car and come upstairs in their Christmas sweaters, though Dean had added a dress shirt and tie under his. He’d explained that he had wanted to look nice since this was a new job for Sam, and it was important to him to make a good impression on his behalf.

“Wow, there are a lot of people here,” Dean commented as he looked around. “You work with all of them?”

“No, this is all three offices from this state, or that’s how it was explained to me. So most of these people, I have no idea who they are.” Sam chuckled softly.

“There sure are a lot of dangly things,” Dean complained as one of the silver spirals that had been pinned to the ceiling smacked him in the eye. Sam narrowly dodged a different one.

“Yeah, I have no idea who thought they were a good idea.”

“Ok, so I guess that’s where you put your potato salad,” Dean nodded towards a table filled with various foods. “But what are we doing with this?” He held up the gift bag with the Secret Santa gift Sam had made his carry. That part was only for the people in Sam’s office. 

“Let me find out.” Sam stopped Andy, the guy that sat at the desk next to his and asked where those gifts went. He was directed to Castiel’s office.

“Ask the boss man to unlock the door. We put them in there since a couple years ago someone stole a bunch of the gifts. Castiel will lock the door again until our office gathers later to swap.” Andy explained.

“Thanks,” He looked around for Castiel and unsurprisingly, found him sitting in a chair in the far corner, a glass of what looked like eggnog in one hand and a slight frown on his lips. He seemed lost in thought and wasn’t really paying attention to anyone around him. So Becky had been right. That was really sad. 

He directed Dean towards the food table where they left potato salad, then he started in the direction of where Castiel was sitting. Dean still had the gift so he followed after him.

“Uh, Castiel?” Sam said the man’s name, half expecting him to be too lost in his own thoughts to hear him, but the moment his name was spoken he looked right at him. He sat up straighter and forced a smile onto his lips.

“Hello, Sam, are you enjoying yourself?”

“We actually just got here. Andy said I should come and ask you to put the Secret Santa gift in your office.” Sam replied. Castiel set his glass aside and tugged his sweater down so his shirt was covered. He noticed the man standing half behind Sam and leaned around him to see him better.

“Hello, you must be Sam’s brother. I’m sorry, I’m not sure he gave me your name. I’m Castiel.” He offered his hand. Dean smiled as he stepped out from behind his brother to shake it.

“I’m Dean. He says nothing but good things about your company and about you as his boss. He says you’re the best he’s ever had.”

Castiel looked surprised by that, but the smile he gave Sam was warm and genuine. “I’m so glad you like working here. It’s wonderful having you as an employee as well. You have no idea how much I appreciate the fact that you get your work done in a timely fashion, even with people talking to you. I never have to worry that you won’t get yours done.” He pulled his keys out and motioned for them to follow him. He unlocked the door long enough for Sam to add his gift to the pile on the floor in the corner, and then he was locking it again.

“So, what is it that you do, Dean?” He asked as they headed back upstairs.

“I’m a teacher,” Dean replied. “Middle school history.”

“Really?” Castiel looked at him and smiled. “I only just learned earlier this week that Sam had a brother. I enjoy getting to know everyone in the office but we haven’t had much time to chat lately, this is our busy season.”

“That’s what he was telling me. I invited him out a few times for lunch on Saturdays but he said he had too much work he was trying to catch up on.”

“We’ve all pulled Saturdays,” Castiel nodded. “But it will start slowing down in a few weeks. By March it will be back to normal.”

They stepped into the conference room again and this time it was Castiel that was smacked in the head by the dangling, paper decoration.

“Jesus,” He muttered as he rubbed the corner of his forehead. “That shouldn’t have hurt.”

“One got me in the eye before,” Dean chuckled. “I think maybe a short person hung them. We’re all over six feet so we’re at eye level with them.”

Castiel smiled and nodded. “Yes, I think Becky and Nathalie hung them.”

“Sam!” Eileen was waving him over. 

“Excuse me,” Sam took a step away before stopping to look at his brother. “Will you be ok on your own for a few minutes?”

“Sure, I’ll be fine,” Dean shooed him away. Sam gave him a quick smile before weaving through the crowd to reach the woman that had been calling his name. 

“Would you like to sit? Or would you rather socialize? I’ll let you be in that case.” Castiel asked.

“I don’t know anyone here,” Dean confessed. “Except maybe you now. I’d rather come sit with you, if that’s ok.”

“Of course,” Castiel seemed pleased by his answer and it had Dean wondering if, despite being surrounded by everyone at the party, he was lonely. “Would you like some eggnog? I’ll warn you though, it’s spiked. Not as badly as in years prior, but there is alcohol in it.”

“Sure, I’ll have a glass,” Dean followed him to the table of food and waited for Castiel to pour him a glass. Once he had it in hand he followed him back to his little table in the corner.

“You and Sam are close I take it,” Castiel said as he settled back in his seat and picked his glass up again.

“We are,” Dean nodded. “He’s my bratty kid brother, but he’s my best friend too.”

“That’s the relationship I have with my brother, except he’s older than me. I also have an older sister and three younger sisters. Being the only boys, I suppose that made us closer, but really, I’m the only one that can tolerate him in larger doses.” Castiel laughed. Dean grinned and chuckled.

“I sometimes feel the same way about Sam.”

“Middle school history, would that be social studies then?” Castiel asked.

  
“No, actually. Middle school is not like it was when we were kids where all we took was social studies. I actually teach two different classes: World cultures and geography, and Civics, government, and economics.” Dean explained. Castiel paused in taking a sip of his drink to stare at him, slack jawed and in shock.

“They are  _ not _ teaching middle schoolers  _ civics _ , are they?”

“Sure are,” Dean took a sip of the eggnog and coughed. This was  _ less _ alcohol than in previous years? “And my students are bright. They’re all doing really well this year.”

“I didn’t take civics until college,” Castiel told him. “My high school didn’t offer it. I enjoyed it though.”

“I did too,” Dean said. “I love history though and I’ve taught it across six different grades over the last twelve years.”

“That’s amazing. I wanted to teach when I was a kid but I don’t think I’d have the patience for it.”

“Is this what you wanted to do?” Dean asked.

“Nah, who says they want to grow up to manage the mortgage side of a bank? There were so many other things I wanted to do. I have a degree in English, because I wanted to be a writer but my parents told me to be practical, so they convinced me to get a degree in business. I’ve put  _ that _ degree to good use at least.”

“Have you written anything?” Rather than take another sip Dean set his glass aside. It was way too strong.

“Well...yes, but it’s not very good.” Castiel admitted.

“Is that just  _ your _ opinion or have you gotten anyone else to read it?”

Castiel was quiet for a moment before laughing awkwardly and shaking his head. “No, I’ve never let anyone read what I’ve written. I suppose I should if I want to find out if it’s any good. I guess I’m just worried it will suck, and then that fantasy of having a book published will pop and this will be all I have.”

“You know, if it’s not as good as you hope, you can always rewrite it,  _ and _ you can ask other writers for guidance and help. You don’t have to take what someone else says as the gospel truth. Ask someone to read something you’ve written, get their honest opinion, and then ask someone else. I’d ask someone without any bias, so probably not close friends or family, they tend to try and be supportive and say it’s good, even if it’s terrible.”

“Mm, maybe you’re right,” Castiel mused. “I’ll think about that later,” He noticed the lack of a wedding ring on Dean’s hand. Sam didn’t have one either. “Did Sam pull you away from your family this evening to come with him?”

“I don’t live with my parents so I wouldn’t have been home with them. Oh, you’re asking if I’m married,” Dean smacked his own forehead and laughed. “Sorry, I don’t know what I was thinking just now. I’m not married, no kids, just me and a couple of sad houseplants.”

“It’s fine. Some of the employees will bring siblings with them, but on occasion they’ll bring some in-laws or friends with. I know most of the people that were brought, because they’ve been brought along to other gatherings, but Sam’s new, so I wasn’t sure if he was bringing anyone, until I asked.” Casitel explained.

“Is your family here? Did you bring someone?” Dean looked around but there wasn’t anyone near them. 

“No, I don’t bring anyone,” Castiel replied quietly. Dean turned around to look at him. There was something in his tone that bothered him. Whoever the someone he wasn’t bringing was, they’d hurt the man badly.

“I see a couple of people brought older children with them.” He said to change the subject. Castiel looked around and spotted the people he was talking about.

“Yes, those are people from the Evansville office, I believe. It’s a long drive up here and I don’t think they wanted to make the trip alone. Bringing the entire family usually isn’t an option. It can get complicated I suppose.”

“Probably.”

“Do you have children?” Castiel asked. Dean shook his head.

“No, no wife, no husband, no kids, not even a pet turtle.”

“Just the sad houseplants,” Castiel teased. Dean laughed and smiled.

“Yes, just them. I think maybe they’re doing a little better, I put a plant bulb in a lamp and set it near them so they’re getting more UV light during the day. They don’t look as droopy as they did.”

“I have a few houseplants, but I have to keep them on the sun porch or hang them up high because I have cats. If they got access they would eat them. One of those plants I’ve had since college.”

“Well, hopefully mine survive. Sam insists the light will help, he says he does that with his plants in the fall and winter. Hey, I’m not monopolizing your time, am I? I don’t want to keep you if you wanted to go talk to people.”

“No, you’re not monopolizing my time. In fact, this is the nicest conversation I’ve had with anyone in months. I suppose I scare my employees, especially around this time of year.”

“Rough time of year?” Dean figured. Castiel smiled softly and nodded.

“I’m sure someone will bring it up to Sam who will in turn mention it to you. I was left at the altar three years ago. Perfect, snowy, Christmas wedding...and he never showed up. I never heard from him again, actually, though for his sake, that’s probably a good thing.” 

“What a douche!” Dean exclaimed. Castiel chuckled before sighing and nodding.

“I think it was probably a good thing he did that. I keep thinking it would have been a miserable marriage, he was very narcissistic.”

“Then be glad he ran. You’re better off without him. His loss though, because you’re really nice.” Dean took another sip of his eggnog, having forgotten how strong the rum in it was. He coughed again as he set the glass down.

“Thank you. People around here walk on eggshells around me in the late fall and early winter . I’m not bitter, not really, but Christmas is always a reminder to me that I’m alone. When I go home for the holidays every one of my siblings has a spouse and kids. I’m the only one that doesn’t. I don’t miss him, good riddance, you know? But I have to hear from every direction questions about how I’m doing, like they expect me to still be sobbing in a corner missing him, or they want to know why I haven’t moved on, which I have, they just don’t see it as moving on because I’m not seeing someone. Then they feel sorry for me, or they offer to set me up with someone they know. By the time Christmas has come to an end I’m exhausted and being cranky is unavoidable. So I’m cranky in the weeks leading up to going home.”

“They love you...but they frustrate you, right?” Dean knew he’d hit the nail on the head. Castiel was nodding, his smile growing wider.

“Yes, exactly. If I have to field one more “Honey, why aren’t you dating? You’re so handsome, I just know there are men out there that would jump at the chance to go out with you” from my mom I think I’m going to scream.”

“Do we have the same mom?” Dean joked as he motioned between them. “Because mine says the exact same thing. My dad will tell her to lay off, but the moment  _ he _ gets me alone he’s asking me if I’m seeing anyone, and if I say no, because I’m not, he wants to know why. I can’t win.”

“Then you understand my frustration,” Castiel smiled softly at him. He was looking at him, actually seeing him and Dean liked that. “You look very nice. I’m glad I’m not the only one that wears a button down and tie under a sweater. I debated on whether I wanted to go with an ugly sweater or not this year.”

“You look sharp, that’s definitely not an ugly sweater,” Dean commented. “The blue is almost the same shade as your eyes. You look really good.”

Castiel blushed and lowered his eyes. He was smiling shyly though. “Thank you. This is my favorite sweater.”

“I have several holiday sweaters and I started wearing a different one each day in December leading up to winter break. This isn’t one of them though. Those are pretty obnoxious, but I wear them on purpose. The kids like seeing me in the tacky sweaters. I save some nice ones for events like this.” He smoothed his fingers down his tie, making sure it was still tucked in.

“You look amazing,” Castiel blushed even more. “I like the powder blue with the snowflakes.”

Dean smiled at the compliment. He leaned an elbow on the table and angled himself towards the other man a bit. “Hey, Cas? Would you like to have dinner with me? Maybe tomorrow night?”

Castiel’s eyes widened. “Really? I mean, I’d love to.”

“Awesome,” Dean’s smile grew bigger. “You’re really easy to talk to, and like, ridiculously handsome. I couldn’t  _ not _ ask, I’d leave tonight kicking myself if I didn’t do it.”

“Thank you for the compliment, Dean,” He didn’t think he’d smiled this much in years, but he felt lighter, happier than he had in as much time. “You’re very handsome as well. If I didn’t know any better I’d have thought you were a model, not a teacher. In fact, I was shocked when you said teacher.”

“I don’t brag, what’s the point? It was a job, it got me through college, but I did model, and for several big named companies. I used the money to pay off my student loans before they came due. Sam modeled too. Once he found out how much money I was making and that I graduated without any debt he asked me how to get into it. I put him in touch with my agent and that’s how he paid his way through college too. We had scholarships but they didn’t cover everything. College is expensive and those bills add up real quick. Sometimes it comes down to the textbook for your biology class  _ or _ food in your stomach. Modeling put food in my belly and paid for most of my courses after whatever the grants and the scholarships covered.”

That launched a conversation about modeling, and then about the different courses they’d taken for their degrees. People kept glancing over at their table curiously, everyone wondering who the man in the baby blue sweater was, and how it was that he had their miserable, cranky boss laughing and smiling so much. June from accounting walked up to Becky and nudged her arm. 

“Who’s the hottie with the boss man?” She asked around a mouthful of sugar cookie. Becky glanced at her, and at the snowman cookie in her hand before looking at Castiel.

“I’m not sure exactly. Castiel was moody as always and the next time I looked over there he wasn’t alone. Whoever he is, he’s a blessing. I haven’t seen him this happy in years.”

“Think the new guy’s single?” June repositioned her headband which had reindeer antlers with lights on it. Her sweater had Rudolph on it too.

“I don’t know, but I get the feeling he’s not straight.” Becky replied. She tapped the arm of the first person to walk past her; Sam Winchester. “Hey, Sam? Do you know who Castiel is talking to?”

Sam looked past her at the table and smiled. Their boss looked very happy. “Yes, that’s my brother, Dean.”

“Is he single?” June asked.

“He’s gay, sorry.” Sam patted her arm before walking away.

“Damn.” June muttered. Becky snickered softly and looked at their boss again. 

“Well, it seems like they like each other. Boss man deserves to be happy. I don’t think he’s really been since Balthazar left him.”

“True. Aww, look how cute they are!” June gushed around the cookie she’d just stuffed in her mouth and gestured as discreetly as possible towards their boss and Dean. Castiel had a hand on Dean’s knee as he leaned towards him. Whatever they were talking about, they were both laughing.

There was plenty of buzz around the office throughout the rest of the party and for weeks afterwards as they learned through Sam that their boss and his brother were dating. Everyone was glad to see Castiel happy again, and not taking his anger and irritation out on them. 

The following year’s Christmas party was much the same, except Dean accompanied Castiel instead of his brother, and they mingled instead of sitting alone in the corner. There wasn’t a Grinch in the office anymore, and that made everyone happy.

And yes, Sam won the TV, much to Zach’s irritation. 


End file.
